Triethylamine → HCID 58451282, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of bis(trichloromethyl) carbonate (30 mg, 0.102 mmol) in tetrahydrofuran (2 mL) was added dropwise a suspension of N—[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.290 mmol) produced in Example 16(vi) and triethylamine (80 μL, 0.580 mmol) in tetrahydrofuran (2 ml) at 0° C., and the mixture was stirred at 0° C. for 30 min. 1-[3-(Trifluoromethoxy)phenyl]methanamine (59 μL, 0.348 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (20 mL), and washed successively with aqueous sodium hydrogen carbonate solution (15 mL) and saturated brine (5 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=50/50→80/20), and the obtained solution was concentrated under reduced pressure. The obtained residue was recrystallized from tetrahydrofuran (3 mL)/ethyl acetate (2 mL) to give the title compound (85 mg, 52%) as a white solid.

Provenance & Evidence